Also, let's not confuse "startup", a single project requiring one's all, with "ventures", a diverse portfolio of small businesses seeded with one's capital but managed and run by domain experts.
Personally, I think the finger in many pies approach is far more interesting and rewarding, since you're hedging your bets.
Just to be clear about one thing: even in successful VC-funded companies with actual exits, 50MM is an anomaly. I have a bunch of friends who have sold companies, and in the crazy-talk best case, one of them got ~$10MM, and it wasn't his first 7+ figure win.
The companies that go for mid/high 8 figures are all apparently VC-funded, most for multiple rounds, meaning that any given founder might be hovering near single-digit points of equity.
Going after a "fuck you" $50MM payday seems like an awfully bad idea. It's not going to happen.
